Lithium Hydroxide → HCID 52914640, compound

HRID 2177670Notes

Reaction equation

HRID 2177670 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([O:19]C)=[O:18])=[C:15]([O:21][CH3:22])[C:14]([C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+]>CO>[C:1]1([S:7]([CH2:10][C:11]2[C:16]([C:17]([OH:19])=[O:18])=[C:15]([O:21][CH3:22])[C:14]([C:23]3[S:24][CH:25]=[CH:26][N:27]=3)=[CH:13][CH:12]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67107589HCID 67107589, compound2×

Product 1

HCID 52914640HCID 52914640, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 6-benzenesulphonylmethyl-2-methoxy-3-(thiazol-2-yl)benzoate (Intermediate 34, 0.1 g) and lithium hydroxide (1M aqueous solution, 1.25 ml) in methanol (2 ml) was stirred and heated at 80° C. for 2 hours. The solution was evaporated to dryness and the residue was purified by HPLC (C18) eluting with a mixture of methanol and water containing 0.1% formic acid, with a gradient of 4-98%. The resultant gum was triturated with ether and the solid was collected by filtration to give 6-(benzenesulphonylmethyl)-2-methoxy-3-(thiazol-2-yl)benzoic acid (0.025 g) as a pale pink solid.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue was purified by HPLC (C18)
  3. washeluting with a mixture of methanol and water containing 0.1% formic acid, with a gradient of 4-98%
  4. customThe resultant gum was triturated with ether
  5. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-ea73e3b4e989441c843073aff6904a06
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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